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Benzyl primeveroside
- Family: Plantae - Solanaceae
- Kingdom: Plantae
-
Class: Glycoside
- Subclass: Benzyl Glycoside
| Canonical Smiles | OC1C(O)C(COC2OCC(C(C2O)O)O)OC(C1O)OCc1ccccc1 |
|---|---|
| InChI | InChI=1S/C18H26O10/c19-10-7-26-17(15(23)12(10)20)27-8-11-13(21)14(22)16(24)18(28-11)25-6-9-4-2-1-3-5-9/h1-5,10-24H,6-8H2 |
| InChIKey | WOGBNISMMIOPAZ-UHFFFAOYSA-N |
| Formula | C18H26O10 |
| HBA | 10 |
| HBD | 6 |
| MW | 402.4 |
| Rotatable Bonds | 6 |
| TPSA | 158.3 |
| LogP | -2.53 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 402.15 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cestrum parqui | Solanaceae | Plantae | 142762 |
Showing of synonyms
Benzyl primeveroside
Benzyl b-primeveroside
MLS000876754
MEGxp0_000053
CHEMBL1371061
ACon1_001508
HMS2269N22
NCGC00180432-01
SMR000440567
BRD-A42757376-001-01-6
Benzyl alcohol beta-D-xylopyranosyl (1->6)-beta-D-glucopyranoside
- Mosad R, Ali M, et al. (2017). New cytotoxic steroidal saponins from Cestrum parqui. Phytochemistry Letters, 2017, 22, 167-173. [View]
No compound-protein relationship available.
SMILES: c1ccccc1COC(O2)CCCC2COC3CCCCO3
Level: 2
Mol. Weight: 402.4 g/mol
SMILES: O1CCCCC1COC2CCCCO2
Level: 1
Mol. Weight: 402.4 g/mol
SMILES: c1ccccc1COC2CCCCO2
Level: 1
Mol. Weight: 402.4 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 402.4 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 402.4 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.59
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -4.71
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.15
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.86
- Plasma Protein Binding
- 2.21
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.62
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.97
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.25
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.51
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -8.33
- Rat (Acute)
- 1.95
- Rat (Chronic Oral)
- 3.69
- Fathead Minnow
- 2.87
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 446.26
- Hydration Free Energy
- -12.98
- Log(D) at pH=7.4
- -0.24
- Log(P)
- -1.89
- Log S
- -1.24
- Log(Vapor Pressure)
- -13.23
- Melting Point
- 165.85
- pKa Acid
- 6.14
- pKa Basic
- 3.53
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.9368 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 4 | 0.9252 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8861 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.8723 |
| Disintegrin and metalloproteinase domain-containing protein 17 | P78536 | ADA17_HUMAN | Homo sapiens | 3 | 0.8655 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.8565 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8542 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8173 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7845 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7758 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7736 |
| Purine nucleoside phosphorylase | Q8I3X4 | Q8I3X4_PLAF7 | Plasmodium falciparum | 3 | 0.7736 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7684 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7675 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7613 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7613 |
| Cytosol aminopeptidase | O86436 | AMPA_PSEPU | Pseudomonas putida | 3 | 0.7496 |
| Lethal factor | P15917 | LEF_BACAN | Bacillus anthracis | 3 | 0.7496 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7490 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7421 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7406 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 3 | 0.7398 |
| Lethal factor | P15917 | LEF_BACAN | Bacillus anthracis | 4 | 0.7365 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7336 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7330 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7218 |
| Periplasmic pH-dependent serine endoprotease DegQ | P39099 | DEGQ_ECOLI | Escherichia coli | 4 | 0.7207 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7187 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 2 | 0.7184 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7163 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7156 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7155 |
| M17 leucyl aminopeptidase | Q8IL11 | Q8IL11_PLAF7 | Plasmodium falciparum | 3 | 0.7098 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7060 |
| Acidic phospholipase A2 3 | P60045 | PA2A3_NAJSG | Naja sagittifera | 2 | 0.7035 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 2 | 0.7033 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7028 |
| Fructose-1,6-bisphosphatase 1 | P09467 | F16P1_HUMAN | Homo sapiens | 2 | 0.7020 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 2 | 0.7002 |